


First Time

by herbivoredinosaur



Category: Supernatural
Genre: Consensual Sex, Crack, Dean Winchester is a God, F/M, Face-Sitting, First Time, Loss of Virginity, Oral Sex, Plot What Plot/Porn Without Plot, Shameless Smut, Smut, Strangers, Vaginal Sex
Language: English
Status: In-Progress
Published: 2020-11-06
Updated: 2020-11-06
Packaged: 2021-03-08 17:27:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,584
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27420424
Author URL: https://archiveofourown.org/users/herbivoredinosaur/pseuds/herbivoredinosaur
Summary: Dean Winchester takes your virginity. It's hot. That's it.
Relationships: Dean Winchester/You
Comments: 1
Kudos: 51





	First Time

**Author's Note:**

> So I said I had no more stories to give and then I found this in a deep dark corner of my laptop. Enjoy! 
> 
> I will write the next chapter at some point promise :)

You never expected this. Not in a million years. Maybe even more than a million years. Things like this didn’t happen to you. Things like _him_ didn’t happen to you.

You were just out at a bar with some friends, your local place for a few drinks after work when he appeared out of nowhere and took you by complete surprise while you were ordering a round for your table. He was a smooth talker, like he could talk to just about anyone and for some reason he was talking to you. Typical you, you stumbled over a few words initially, always a little unsure of yourself but eventually his calm demeanor seemed to work, and you even managed to string a few proper sentences together.

He paid for the round, insisted on it and then you left with blushed cheeks and a stupid smile on your face. You carried the drinks over to your friends who were appalled you had left something like _that_ over there on his own when he clearly wanted you. You laughed it off, not buying it, not really anyway. People like him didn’t talk to people like you in that way, not in the way they were insinuating. He was just being friendly.

Your friends refused to let this up. It was apparently a perfect opportunity to lose a certain card that you had been stowing away for safe keeping.

“You need to pop your cherry Y/N and he’ll do the job just fine.”

“More than fine, he is smoking hot. I bet he’d be amazing at sex.”

“And he’s a stranger, no strings attached. Have sex with him and then it’s done.”

“He doesn’t even need to know you’re a virgin.”

“He keeps looking back, it’s totally a sure thing.”

“Go back and woo him girl!”

Going back to him was more out of getting them to shut up rather than thinking you had any hope of getting this guy to sleep with you. Your friend was right, he was smoking hot, all kinds of hot and you were just…well you. Not to mention a virgin with little to no experience in this department whatsoever. Someone like him would have plenty, more than plenty. Girls and guys probably fell over themselves to even get a chance to get him in bed and for some reason your friends were convinced you had a shot.

Least you could say you tried.

* * *

Dean walked you back to his motel room. You figured a bit safer than your own place, not that he gave off a serial killer vibe. Your friends all gave you the thumbs up when you left the bar. Sweat gathered in your palms as you walked beside him. This was happening, or at least this was going in the way that it could be happening.

“You alright there, Y/N?” He asked noticing you were fidgeting with the sleeve of your jacket. You stopped it, shoving your hands into your pockets.

“Yep, fine, completely fine.” You replied quickly. You flashed him a smile to hopefuly ease his worries. Dean looked like he almost bought it, almost. When you were at the front door, he took your waist, guiding you to rest your back against it.

You gulped, eyes wide staring up at him.

“I’m pretty good at telling when people are lying,” He said. He lifted his hand up to your face, letting the back of his knuckles touch your cheek lightly. “If you don’t want to do this…”

“I do.” You interrupted him. Your friends’ words ringing in your mind.

_Have sex with him and then it’s done._

_You need to pop your cherry._

Three beers gave you enough courage to get on your toes to kiss him. You had done that enough times to know how it worked, not a master of lip locking but you could hold your own. Dean’s bowed lips slotted between yours with ease. You could feel him smile against your lips before he tilted his head to get a better angle. When his tongue touched yours, you could taste the beer off of him.

Dean pulled back to speak against your lips, “How about we go inside?”

You nodded, licking your bottom lip. Inside sounded equal parts terrifying and exciting.

He unlocked the door and once inside Dean pushed you up against the door, stealing your breath away with his hot mouth and skilled tongue. You felt a little lightheaded, trying to keep up with him. Hands reaching for his biceps to steady yourself even though his were gripped tight to your hips.

You were going to have sex. You were going to have sex with Dean. This gorgeous man with his smooth talking and wicked smile and _ohmygod_ that’s an erection pressing against your stomach. Your brain short circuited.

“Wait, wait, wait!”

“What?” Dean took a step back, eyes darting over you like he just stabbed you or something. “Did I do something…”

“I’m a virgin!” You blurted out before really thinking about it. His erection startled you, more so than you realised. You never been around one, never felt one, never had one pressed against you and as far as you could remember never been the cause of you.

Dean’s face dropped. The mouth that was on yours, now slightly gaping to match his shocked expression. He hadn’t planned on bringing back a virgin. Why would he? It’s not like you were some teen, you were an adult, an adult you hadn’t even gotten laid yet because you were what? Too scared? Frigid? He brought you back to get laid, a fuck, not to have to deal with a virgin, not to have to deal with _you_.

“I’m sorry. Oh God this is so embarrassing, I’ll just go and…” you had your hand on the door handle, ready to leave and drown your embarrassment in tequila when his own hand wrapped around your wrist.

“Hold up sweetheart,” Dean stopped you in your tracks, “Don’t go on my account.”

“But, what I said, what I am,” you couldn’t even look at him. No doubt your cheeks were a whole new shade of red than they’d ever experienced. “It’s not what you want.”

Dean tried to turn you around. You went, though your eyes stayed fixed to the crappy carpet beneath you. The back of his hand went to touch your chin, silently asking you to lift your head. You resisted.

“Y/N, there aint nothing wrong with being a virgin.”

Those words startled you. You raised your head, meeting soft green eyes and a warm smile.

He pulled you over to the bed. You both sat on it, shoulders touching. Dean ran his palms up his thighs. It was awkward. This whole thing was awkward. Why did you have to tell him? You could be having sex right now. You could be losing your virginity and maybe Dean would have just thought you were out of practice rather than never even entered the game.

“Not gonna lie, been a while since I’ve taken someone’s virginity.”

“Wait,” you looked over at him. “You’re considering it?”

“I mean, that’s why you’re here right? Cashing in that V card of yours which to be honest I’m surprised you still have. You’re gorgeous.” He replied.

You smiled, eyes down cast at your hands as you spoke, “I was waiting for the right time…”

“Hooking up with some random guy in the bar is your idea of the right time?” he asked with a chuckle. You glared at him with unimpressed eyes.

“No smartass,” you nudged him with your shoulder, “The right time never showed up.”

Dean nodded understanding the situation better.

The silence was all kinds of deafening. Your brain started to fill it with bad thoughts, thoughts that Dean was just trying to be kind, trying to figure a way for you to leave so he doesn’t have to deal with you and avoid hurting your feelings.

“You don’t have to Dean. I mean I can still go, and we can forget this ever happened. Maybe you can still hook up with someone, the bar is open and…” you started to rise again, eyes on the door, on a way out of here.

“Will you quit trying to get yourself out of this? I’m not saying no. I’m thinking about it. Sit down and shut up for a second.” Dean snapped. He pushed you back down by your shoulder and you went. The springs bounced underneath you.

This time you stayed quiet till he spoke, which felt like forever but was probably another minute or two max. Your virginity was in his hands, sort of.

“We’ll take things slow, real slow.” Dean said.

You gulped back the dryness in your throat. He was going to do it. He was going to have sex with you, going to take your virginity. He was going to take your virginity and know that he was going to take it when he could have a well experienced person for his one night passing through.

“Ok.” You replied quietly, like the fear of saying anything might actually make him change his mind. You had a habit of speaking before thinking, letting your emotions run your mouth. This wasn’t new to him though, having blurted out your virginity within the first instance of anything beyond kissing happening.

Another moment passed, then Dean reached for your face, turning it to face him. You felt a rush of heat run through you when your lips touched again, this time he was gentle, so soft and fragile, like kissing a rose petal. To steady yourself you put your hand on his thigh, listening to your body and leaning into him wanting more.

He took your waist and you straddled his lap, letting your hands go up to run through his hair, enjoying the feel of it through your fingers. You could do this, this was good, really good and it seemed like Dean was ok with it too, letting you decide when to take this further. The tight grip on your waist previously now replaced with more gentle touches.

You broke the kiss, a little breathless and flustered. Dean looked at you, mouth glistening from your shared kisses. Whatever he thought about you being gorgeous, he was next level.

“Can I ask you something?”

“Sure.”

Your ran your hands down the front of his chest. “Why are you doing this?”

“Because I want to,” Dean shrugged. “And if you’re going to lose your virginity, might as well be with someone who knows what they’re doing,” He winked at you which made you smile, easing some tension in you. “Now we can keep talking or we could get this show on the road, whaddya say?” He touched up the hem of your top.

You raised your arms, letting the fabric lift off of you. The chill made you shudder as did Dean’s hands that were running down your back. He rubbed his fingers along your bra strap, and you nodded, letting him undo the fasten with one hand. You helped him take it off, leaving it to drop onto the floor.

Dean took you in, making you self-conscious. You went to wrap your arms around yourself, but he tutted, taking your arms away.

“None of that sweetheart.” He kept your arms by your sides, his hands keeping them there.

You obeyed. You were in good hands. He knew what he was doing.

When he took his hands off of you, you kept them there. He smirked making you blush even more. Dean brushed his thumb over your breast and your breath hitched when he touched your nipple.

“Sensitive?”

“I guess.” You murmured, watching attentively as he rolled your hardening nub between his fingers. You held onto his shoulders, noticing your heart rate picking up.

Dean took the other one next. “You never do this on yourself? Never…”

“Never.” You exhaled, eyes fluttering with the sensation washing over you.

“You telling me you’ve never touched yourself? Ever?” he sounded unconvinced.

You shook your head, embarrassed with the admittance. It always felt foreign to you, like something you shouldn’t do. You knew it should feel good, but you were too ashamed that no one else had ever touched you so you avoided it and then eventually the thought of doing it seemed to wash away as your life went on.

He leaned in to kiss you, like he could sense you were ashamed, which you were. He didn’t want you to feel that way, already picking up that his mouth seemed to distract you enough to quieten your negative mind.

When he pulled back any thoughts you had were non-existent, just you and him, in this moment, in this room. “Don’t worry Y/N, I’ll make it good for you. I promise.”

You believed him.

* * *

Dean took your clothes off piece by piece. He told you to tell him to stop and if you didn’t, he’d just keep going which you appreciated. You stepped out of your jeans and panties in one go. Dean told you to lie down on the bed while he took your socks off. It tickled and Dean nipped at your calf when you giggled.

Next Dean stripped. You watched with hooded eyes. He was even more gorgeous bare, lean chest and stomach, you found yourself salivating from the sight. He kept his boxers on which you raised a brow at.

“I know I’m the virgin here and all, but I think you need to lose the boxers,” you lifted your foot to poke at the black fabric on his thigh. He took your ankle, shaking his head.

“They’re staying on for now,” he said. “There’s a few things I want to you to experience before we get to the main event.”

“Like?” you asked, raising up onto your elbows.

Dean crawled up your body. It created a cascade of goosebumps over you. His eyes darkened as he went, bracketing you in with his arms. You reached to touch his skin. It was cool, unlike your own which was burning up with those eyes on you.

“Like…” Dean licked his mouth before continuing. “I wanna eat you out.”

You nodded instantly and Dean chuckled over you enjoying your eagerness.

He leaned back onto his heels. “On all fours for me, top of the bed.”

You turned, moving up to the top and rising up on all fours like he said. You felt exposed, more than you had when he got you naked. This position was vulnerable, and you couldn’t see him which made you nervous.

“Dean.” You whispered, looking over your shoulder.

“I’m right here,” he touched your thigh, making you spread yourself wider, “Not going anywhere. I told you I’d make it good, didn’t I?”

You nodded, watching him get on his back and shuffle underneath you. His hands went on the small of your back, pushing you down into what you kinda felt was a yoga position.

He kissed the inside of your thigh. “This will be good, just breathe.”

You obeyed, taking a deep breath, filling your lungs then you choked on the air when you felt Dean’s tongue touch your center in one long lick. You raised up higher on instinct, the feeling so unfamiliar to you that you didn’t understand it.

“Shush, its ok, you’re ok,” He assured you. His hands touched your back, sliding them up and down your flanks. “You gotta relax, let me take care of you.”

Another breath filled your lungs. You had to relax. This was going to be good. Being eaten out was supposedly amazing unless your friends were lying all those times guys they’d been with even did it. It seemed to be a rare occurrence and you had someone like Dean willing, even wanting to do it.

You bared down again. Dean kissed the soft flesh on your thigh, like a warning of what he was about to do. This time when his tongue pressed you welcomed it, breathing through the sensation. It started off strange, then the more he licked strips the feeling changed. Your folds parted and he kissed your clit, sucking it into his mouth and releasing it with a smack.

“Oh fuck,” you cursed, rolling your head into the pillow beneath you, “Fuck, Dean, _Dean_.”

“God you’re so wet already,” He breathed on your cunt and grasped your ass cheeks making you let out a desperate whine. “You want some more?”

“Yes,” you spread yourself more. “More, please I want more.”

Dean brought you down further, his mouth latched onto your cunt, almost making out with it. You could hear how wet you were, also how easy it was for Dean’s mouth to move over you. It was hot, so hot and incredible, so incredible. Your legs started to shake with the feeling of his mouth. His hands roamed your body, light fingers touching the knobs of your spine only adding to the overall pressure building inside of you. You’d read enough to figure out what it was.

“Dean I feel…” You were cut off when his tongue dipped inside of you, words replaced by a loud moan. He groaned too, pushing his face further into you, like he was quenching a dying thirst.

 _“Dean.”_ You gasped, you reached down to touch his head, trying to get his attention.

He released you. “What is it?”

“I think I’m gonna cum.” You panted, trying to get your words out.

He chuckled. “That’s what I was going for Y/N.”

“But we haven’t even had sex yet!” _And I’m gonna die before we even get to it._

“Don’t worry,” Dean lapped at your clit as he spoke, “If I fuck you right, you’ll be cumming then too.”

Dean’s words did things to you, well, Dean’s everything did things to you but hearing that he was going to fuck you, make you cum twice was overwhelming. You moaned into the pillow, taking a hold of it to hold on as your arms started to ache holding yourself up. Dean’s mouth was back on you, tongue swirling over you and you were wet, so wet, you could hear it over the pounding of your heart.

He concentrated on your clit, knowing that’s where he got your loudest moans and it was true, your whole body quaked when he touched you there, pressing hard against it, sucking it between his plump lips. That pressure kept building, starting in your center and working its way over you.

When you felt it get too much you weren’t sure if it was supposed to be this intense because ohmygod this was a lot. It kept coming, kept building and your voice started to crack, gasping for air that was getting hard to fill your lungs. Part of you wanted this to stop but you kept going, kept going towards that orgasm till your body convulsed and it was too much and you tried to rise your hips but Dean stopped you, holding you down with his strength and keeping his mouth on you.

“Dean!” you cried when it finally hit you like a punch in the gut. You saw stars as your orgasm rode over you in strong waves. Your hips started to roll, wanting more, needing more of those waves, chasing it on Dean’s mouth who was more than happy to provide it. He groaned, shoving his face further into you, lapping up all you gave him. His hands like clamps on your hips and it was mind-blowingly good.

Eventually you came down to earth, letting out a big sigh and your body started to go slack. Dean noticed it, easing up his grip and releasing his mouth.

“Fuck Y/N, that was incredible.” He said, his voice strained and started to move away from you. You let your body drop and rolled over, wanting to see him.

“You’re incredible.” You replied half-heartedly, still blissed out from your first ever orgasm.

He wiped at his face, but you managed to catch the glisten of yourself on him. You lifted your hand out and Dean leaned in letting you swipe your thumb on a section he missed. Bringing it to your mouth you tasted yourself, unsure of what to expect but the reaction on Dean’s face made you think it was the right idea. His brows furrowed, mouth gaped and then he was on you in a flash, diving his tongue into you.

You opened your mouth and the small taste you had was replaced with all of you, on his tongue, in his mouth and you sighed at the taste, trying to get more of it out of him. That mouth was on you, inside of you and made you cum and for some reason you felt like this was you thanking him. Your hands dug into his scalp, holding him there till your mouth hurt.

Dean moved to kiss your neck, behind your ear that was unexpectedly arousing. You gasped as he pulled your skin into his mouth, seeking out more by bearing your neck. You hoped the mark would last, a reminder of this night for days to come. Your brain caught up with you eventually, reminding you that you weren’t finished yet.

“What now?” You asked, still a little breathless.

He leaned up, looking down at you. “You tell me sweetheart, what do you want?”

The answer was easy. “I want you to fuck me."

* * *


End file.
